FR2839717A1 - Cosmetic compositions containing nitrogen-substituted chalcone derivatives, useful for protection against UV radiation - Google Patents

Abstract

Cosmetic compositions containing chalcone derivatives (I) are effective as filtering agents for a wide range of UV radiation (UV-A and UV-B), and in depigmentation of the skin. Cosmetic compositions containing chalcone derivatives (I) are effective as filtering agents for a wide range of UV radiation (UV-A and UV-B), and in depigmentation of the skin R1 = NY1Y2 or N=CY1Y2; R2-R9 = H, OH, alkoxy, acyloxy, 1-12C alkyl, NO2, CN, sulfuryl, phosphoryl, Cl, Br, F, silicyl, -O-glycosyl (optionally substituted), 2-30C alkenyl, 2-30C cycloalkenyl, 6-30C aryl, aralkyl, alkylaryl, NY3Y4 or N=CY3Y4; or R2+R3, R3+R4, R4+R5, R5+R6, R6+R7, R7+R8, R8+R9 = a 4-8 membered ring; and Y1-Y4 = H, 1-12C alkyl, 2-30C alkenyl(acyclic or cyclic),6-30C aryl, aralkyl or alkylaryl; or Y1+Y2, Y3+Y4 = a 4-8 membered ring including C, N, O and/or S atoms, optionally substituted or aromatic. An Independent claim is also included for the preparation (I).

Description

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 The present invention relates to a chemical compound consisting of a chalcone derivative. This invention also relates to a filter composition, to a cosmetic composition and to a filtering cosmetic composition comprising such a chemical compound as well as to a process for the preparation and use of such a composition in various fields.

 The present invention relates to the field of the manufacture of chemical compounds and compositions, comprising such a chemical compound, as well as the use of these compounds and compositions, more particularly in the cosmetic field, particularly when it comes to ensuring protection against ultraviolet radiation.

 In this regard, it should be noted that, in a manner known per se, the sun emits radiation among which there is ultraviolet radiation to which the skin and the hair are sensitive.

 It is, more particularly, such ultraviolet radiation whose wavelengths are between 280nm and 400nm which allow browning of the human epidermis.

 However, it should be noted that ultraviolet radiation with wavelengths between 280 and 320 nm, known as UV-B, can cause sunburn, erythema and burns. cutaneous more or less important.

 As for the radiation whose wavelengths are between 320 and 400 nm, known under the name of UV-A, it is likely to induce an alteration of the skin, especially in the case of sensitive skin or skin continuously exposed to the sun, such alteration resulting in a loss of elasticity of the skin and the appearance of wrinkles leading to premature aging of the skin. UV-A rays also promote the initiation of erythematous reactions or amplify such a reaction in certain sensitive subjects and may even be the cause of phototoxic or photoallergic reactions.

 In this respect, it should be noted that in the spectral range of UV-A, ultraviolet radiation with wavelengths between 370 and 400 nm, known as long UV-A, is particularly penetrating and is partly

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 responsible for the development of certain skin cancers and immunosuppression as well as photoviellissement cutané.

 Also, and in order to filter these ultraviolet rays, we already know, on the one hand, of numerous chemical compounds capable of absorbing UV-B radiation and, on the other hand, of hydroxy derivatives of chalcone capable of to filter the UV-A radiation.

 In this regard, it will be noted that such UV filters have many disadvantages.

 Thus, when it is desired to filter ultraviolet radiation over a wide spectral range, it is possible to produce a composition containing substances capable of filtering UV rays over a wide range of wavelengths. It turns out, however, that such substances, on the one hand, are not always sufficiently stable in conventional cosmetic media and, on the other hand, have insufficient photochemical stability.

 To ensure such a filtering over a wide spectral range, it is also possible to achieve a mixture of different chemical compounds which, then, have the disadvantage, on the one hand, of insufficient photochemical and thermal stability (especially in as regards the chalcone hydroxy derivatives) and, on the other hand, not always be sufficiently soluble in the usual cosmetic media, let alone in the same cosmetic medium.

 In addition, it should be noted that among the commonly used filtering chemical compounds, especially those mentioned above, there are no truly effective organic filters in the spectral range of long UV-A corresponding to wavelengths of 370 nm at 400 nm so that in this range of wavelengths, the sun protection is not ensured.

 The present invention is intended to overcome the disadvantages of chemical compounds and compositions of the state of the art.

 In this regard, the Applicant has discovered a new family of chemical compounds consisting of nitrogen derivatives of chalcone and has developed new processes for obtaining these chemical compounds. The Applicant has also unexpectedly and surprisingly discovered that these nitrogen derivatives of chalcone have, on the one hand, very good filtering properties with respect to radiation.

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 ultraviolet, this over a particularly wide range of wavelengths from UV-B to UV-A long and, on the other hand, an insolubility in water and excellent solubility in common solvents including fats and, on the other hand, a very good thermal and photochemical stability.

 These chemical compounds of nitrogen derivatives of chalcone have the advantage of being neither toxic, nor irritating, nor harmful (in themselves or associated with agents conferring these characteristics) for the skin and the hair, which authorizes them. use for the preparation of cosmetic compositions, in particular filtering compositions.

 Another advantage of these compounds is that they can be incorporated into compositions, as appropriate, filtering for the protection of a sensitive material against ultraviolet radiation or cosmetics for depigmentation of the skin.

 According to another advantage, such compounds may, again, be incorporated in a preparation for the manufacture of fibers or textile polymers for protection against ultraviolet radiation.

 Yet another advantage is that such a compound can be used for the manufacture of a medicament for the prevention of the harmful effects of ultraviolet radiation.

Also, the subject of the present invention is a chemical compound consisting of a chalcone derivative, characterized in that this compound is defined by a nitrogen derivative of chalcone of general formula:

In this formula (I), R1 denotes either a group NY1Y2 comprising at least one nitrogen atom substituted with two groups Y1 and Y2, or a group N = CY1Y2

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 comprising at least one nitrogen atom and at least one carbon atom substituted with two Y1 and Y2 groups.

 In these groups NY1Y2 and N = CYiY2, Y1 and Y2 may denote, independently of one another: a hydrogen atom; a saturated or unsaturated, straight or branched chain C1-C12 alkyl group; a C 2 to C 30 alkenyl group, linear or branched, acyclic or cyclic, optionally interrupted by one or more heteroatoms (in particular of the oxygen, sulfur, nitrogen type) and / or optionally substituted by one or more different groups of a hydrogen atom; hydrogen; an aryl group, an aralkyl group or a C 6 -C 30 alkyloryl group, optionally substituted with one or more different groups of a hydrogen atom.

 In this same formula (I), Y1 and Y2 may together form a ring comprising from 4 to 8 atoms (preferably from 5 to 7 atoms), such an atom being a carbon atom and / or nitrogen atom. and / or oxygen and / or sulfur, such a cycle may be substituted or unsubstituted, aromatic or not.

In the same formula (I), the substituents R 2, R 3, R 4, R 5, R 6, R 7, R 8 and R 9 may denote, independently of one another: a hydrogen atom; a hydroxyl group, an alkoxy group, an acyloxy group, an alkyl group or
C1 to C12 straight or branched chain saturated or not; a nitro group, a nitrile group, a sulfur group, a phosphorus group, a chlorinated group, a brominated group, a fluorinated group, a group comprising at least one silicon atom; a -O-glycosyl group, a -O-glycosyl group substituted with one or more substituents; a C 2 to C 30 alkenyl group, linear or branched, acyclic or cyclic, optionally interrupted by one or more heteroatoms (in particular of the oxygen, sulfur, nitrogen type) and / or optionally substituted by one or more different groups of a hydrogen atom; hydrogen;

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 an aryl group, an aralkyl group, a C 6 -C 30 alkyloryl group, optionally substituted with one or more different groups of a hydrogen atom; a group NY3Y4 or a group N = CY3Y4, in which the substituents Y3 and Y4 (as the case may be, substituting the nitrogen atom or the carbon atom) may either designate independently, on the one hand, of each other and, on the other hand, of R1, any of the above-mentioned Y1 / Y2 atoms or groups, independently of R1, form a ring similar or identical to a ring capable of be formed by these same substituents Y1 and Y2.

 In this same formula (I), the substituents R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9 may, again, be defined so that for at least two of these substituents R 1 and R x + 1 (x = 2 to 8), these Rx and Rx + 1 substituents together form a ring having from 4 to 8 atoms (preferably from 5 to 7 atoms), such a atom being a carbon atom and / or nitrogen and and / or oxygen and / or sulfur, such a cycle may be substituted or unsubstituted, aromatic or otherwise. In this case, the substituents R2 to R9, other than ring-shaped substituents Rx and Rx + i, denote, independently of each other, an atom or group of the aforementioned type for such substituents R2 to R9.

 According to another characteristic of the invention, such a chemical compound of a nitrogen derivative of chalcone, corresponding to the formula (I), comprises a group NY1Y2 or a group N = CY1Y2 which can be in position 2, 3 or 4 on the ring corresponding.

 Thus and according to a first embodiment, such a chalcone nitrogen derivative chemical compound corresponding to formula (I) may be defined by a member of the 2'amino subfamily (wherein the amino group is substituted or unsubstituted) as one of the following compounds: - 2'-amino chalcone; 2'-amino-2-methoxy chalcone; 2 '- (dimethylamino) -2-methoxy chalcone; 2'-amino-2-ethoxy chalcone; 2'-amino-2,3-dimethoxy chalcone; 2 '- (dimethylamino) 2,3-dimethoxy chalcone; 2'-amino-2,4-dimethoxy chalcone; 2'-amino-2,5-dimethoxy chalcone;

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 2'-amino-2,6-dimethoxy chalcone; 2'-amino-2,4,5-trimethoxy chalcone; 2'-amino-2,4,6 trimethoxy chalcone; 2'-amino-2,3,4-trimethoxy chalcone; 2'-amino-5,6-benzo-2-hydroxy chalcone; 2'-amino-5,6-benzo-2-methoxy chalcone; 2 '- (methylamino) -2-methoxy chalcone; 2 '- (methylamino) -2-methoxy chalcone; 2 '- (methylamino) -2,3-dimethoxy chalcone; -2'- (methylamino) -2 chalcone; -2'- (methylamino) -2 chalcone; 2 '- (methylamino) -2,6-dimethoxy chalcone; 2'- (methylamino) -2,4-trimethoxy chalcone; 2'- (methylamino) -2,5-trimethoxy chalcone; 2'- (methylamino) -2,6-trimethoxy chalcone.

 Another embodiment is that such a chemical compound of a nitrogen derivative of chalcone corresponding to the formula (I) can be defined by a member of the 4'amino subfamily such as one of the following compounds: 4'-amino chalcone; 4'-amino-2-methoxy chalcone; 4 '- (dimethylamino) -2-methoxy chalcone; - 4'-amino-2-ethoxy chalcone; 4'-amino-2,3-dimethoxy chalcone; 4 '- (dimethylamino) 2,3-dimethoxy chalcone; 4'-amino-2,4-dimethoxy chalcone; - 4'-amino-2,5-dimethoxy chalcone; - 4'-amino-2,6-dimethoxy chalcone; 4'-amino-2,4,5-trimethoxy chalcone; - 4'-amino-2,4,6 trimethoxy chalcone; - 4'-amino-2,3,4-trimethoxy chalcone; 4'-amino-5,6-benzo-2-hydroxy chalcone; 4'-amino-5,6-benzo-2-methoxy chalcone;

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4 '- (methylamino) -2-methoxy chalcone;
4 '- (methylamino) -2-methoxy chalcone;
4 '- (methylamino) -2,3-dimethoxy chalcone; 4 '- (methylamino) -2,4-dimethoxy chalcone;
4'- (methylamino) -2,5-dimethoxy chalcone; 4 '- (methylamino) -2,6-dimethoxy chalcone; 4 '- (methylamino) -2,3,4-trimethoxy chalcone; 4 '- (methylamino) -2,4,5-trimethoxy chalcone;
4 '- (methylamino) -2,4,6-trimethoxy chalcone.

4-methoxy-4'N- (4-methoxybenylidene) -amino chalcone
Yet another embodiment is that such a chemical compound of a nitrogen derivative of chalcone corresponding to the formula (I) can be defined by a member of the 3'amino subfamily such as one of the following compounds - 3'-amino chalcone; - 3'-amino-2-methoxy chalcone; 3 '- (dimethylamino) -2-methoxy chalcone; - 3'-amino-2-ethoxy chalcone; - 3'-amino-2,3-dimethoxy chalcone; 3 '- (dimethylamino) 2,3-dimethoxy chalcone; - 3'-amino-2,4-dimethoxy chalcone; - 3'-amino-2,5-dimethoxy chalcone; - 3'-amino-2,6-dimethoxy chalcone; 3'-amino-2,4,5-trimethoxy chalcone; - 3'-amino-2,4,6 trimethoxy chalcone; 3'-amino-2,3,4-trimethoxy chalcone; 3'-amino-5,6-benzo-2-hydroxy chalcone; 3'-amino-5,6-benzo-2-methoxy chalcone; 3 '- (methylamino) -2-methoxy chalcone; 3 '- (methylamino) -2-methoxy chalcone; 3 '- (methylamino) -2,3-dimethoxy chalcone; - 3'- (methylamino) -2, chalcone; - 3'- (methylamino) -2, chalcone;

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 3 '- (methylamino) -2,6-dimethoxy chalcone; 3 '- (methylamino) -2,3,4-trimethoxy chalcone; 3'- (methylamino) -2,5-trimethoxy chalcone; 3 '- (methylamino) -2,4,6-trimethoxy chalcone.

 The invention also relates to the various processes for obtaining a nitrogen derivative of chalcone corresponding to formula (I) above.

 In this regard, it should be noted that such a method of obtaining differs, particularly as regards the number of steps in this process, depending on the nature of the group R 1 or the substituents R 2, R 3, R 4, R 5, R6, R7, R8, R9.

However, regardless of R1 to R9, such a process for obtaining comprises reacting an appropriate benzaldehyde of formula (II) with an appropriate nitrogen-containing acetophenone of formula (III) according to the following reaction scheme:

Such a reaction is carried out in a solvent chosen from water, C1-C4 lower alcohols or a mixture of water and these alcohols. This reaction is again in a basic medium comprising an alkaline agent selected from alkali or alkaline earth hydroxides or sodium or potassium alcoholates. The reaction is carried out at a temperature ranging between 0 C and the boiling point of the solvent or of the solvent mixture.

 It should be noted that when the substituents R2 to R9 are OH groups, benzaldehyde or acetophenone must be protected so as to intervene in the condensation process. A complementary step then consists in deprotecting the final chalcone to obtain substituents R2 to R9 consisting of -OH groups.

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 It will be observed, again, that the chemical compounds consisting of nitrogen derivatives of chalcone of formula (I) obtained by these methods of obtaining usually require to be purified.

 In this regard, it will be noted that the purification of these compounds varies according to the group R 1 and the substituents (R 2 to R 9) and that, according to this group or these substituents, it is necessary either to carry out a simple filtration after reaction followed by recrystallization, or to employ a method including washing with water and extraction with an appropriate solvent preferably chosen in solvents such as dichloromethane, chloroform, ethyl acetate.

 The extracted organic phases are concentrated and then resolubilized in a minimum of the extraction solvent and then added with a solvent, which may be a lower C1-C4 alcohol, to crystallize the desired product. This can be recrystallized from the same solvent mixture for better purification.

 The present invention also relates to a filtering composition comprising, in an acceptable support, an effective amount of at least one chemical compound consisting of a nitrogen derivative of chalcone corresponding to formula (I).

 In fact, such a filtering composition is intended to protect a sensitive material against ultraviolet radiation, in particular against solar radiation, for radiation whose wavelengths are between 280 and 400 nm.

 As sensitive materials that may be protected against ultraviolet radiation, mention may be made of makeup products, plastics or fibers such as cellulosic fibers, keratin fibers or textile polymers.

 In order to provide such protection, the invention also relates to a method of protecting such an ultraviolet sensitive material comprising applying to said material an effective amount of a composition containing at least one nitrogen derivative. chalcone corresponding to formula (I).

 The Applicant has surprisingly noticed that the chemical compounds constituted by nitrogen-containing chalcone derivatives according to the invention and corresponding to formula (I) could advantageously be used to provide protection against ultraviolet radiation from a sensitive material such as the epidermis and / or the hairs, more particularly human as the natural hair or

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 sensitized (i.e., having undergone permanent treatment, coloring, bleaching or other).

 Also, the invention also consists of a filtering cosmetic composition for the protection of the epidermis and / or the hairs against ultraviolet radiation, this composition comprising, in a cosmetically acceptable support, at least one nitrocellulose derivative of formula (I) constituting a compound for filtering ultraviolet radiation with wavelengths between 280 and 400 nm.

 Again, it will be observed that such a cosmetic filtering composition can be used in the context of a method for protecting the epidermis and / or the hairs against ultraviolet radiation, such a method of applying to the epidermis and / or the bristles an effective amount of a filtering cosmetic composition containing at least one nitrogen derivative of chalcone corresponding to the formula (I).

 According to a first embodiment, such a cosmetic filtering composition may be intended to be applied to the epidermis and be in the form of: a suspension in solvents or fatty substances (in particular a cream, a milk or the like ); a dispersion, in particular a vesicle, in solvents or fatty substances (in the form of a gel, an ointment, a solid stick, in particular a stick, an aerosol, in particular in the form of a foam or spray); a water-in-oil emulsion or (and preferably) oil-in-water, such as a cream, a milk; - A powder, a lotion, especially thickened, oily or oleoalcoholic type.

 In this connection, it should be noted that such an emulsion may, in addition, contain anionic, nonionic, cationic or amphoteric surfactants.

 According to another characteristic of the invention, a filtering cosmetic composition intended to be applied to the epidermis may, again, contain artificial tanning and / or browning agents for the skin, in particular self-tanning agents.

 Another feature of the invention consists of a filtering cosmetic composition intended to be applied to the bristles, more particularly to the hair, such a composition being in the form of a shampoo, a lotion or a gel

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 or a composition to be rinsed, applied before or after shampooing, before or after coloring or bleaching, before, during or after permanent or straightening. Such a composition may, in addition, take the form of a lotion or a styling gel or treatment, a lotion or a gel for blow drying or setting, a hairspray, d a composition of permanent or straightening, of a coloring composition or discoloration of the hair.

 In fact and according to a first embodiment, a cosmetic filtering composition according to the invention, intended to be applied to the epidermis and / or on the bristles, may consist of a makeup product and may then be present, for example, in the form of a treatment cream for the epidermis and / or hair, a foundation, a lipstick stick, an eyeshadow, an eye shadow. cheeks, a liner still called eyeliner, a mascara, a dye gel or other.

 Such a composition in the form of a makeup product can then be in solid or pasty, anhydrous or aqueous form and be presented as an oil-in-water or water-in-oil emulsion, such as a suspension or a gel.

 According to another embodiment, such a filtering cosmetic composition intended to be applied to the epidermis and / or the bristles may consist of a sunscreen composition and be in the form of: a suspension in solvents or fatty substances (in particular a cream, a milk or the like); a dispersion, in particular a vesicle, in solvents or fatty substances (in the form of a gel, an ointment, a solid stick, in particular a stick, an aerosol, in particular in the form of a foam or spray); a water-in-oil emulsion or (and preferably) oil-in-water, such as a cream, a milk; - A powder, a lotion, especially thickened, oily or oleoalcoholic type.

 The Applicant has, moreover, surprisingly found that a chemical compound consisting of a nitrogen-containing chalcone derivative according to the invention and corresponding to formula (I) could also be used to ensure depigmentation of the epidermis. .

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 Also, the present invention relates, again, to a cosmetic composition for the depigmentation of the epidermis, characterized in that it comprises, in a cosmetically acceptable carrier, at least one nitrogen derivative of chalcone of formula (I). Such a cosmetic composition can then be used during a process for the depigmentation of the epidermis consisting in applying to this epidermis an effective amount of a cosmetic composition containing at least one nitroceared chalcone derivative of formula (I) .

 According to another characteristic, such a cosmetic composition for the depigmentation of the epidermis may be in any galenical form normally used for topical application of this type, especially in the form of an aqueous, hydroalcoholic or oily solution, a oil-in-water or water-in-oil or multiple emulsion, an aqueous or oily gel, a liquid, pasty or solid anhydrous product, an oil dispersion in an aqueous phase with the aid of spherules, these spherules may be polymeric nanoparticles such as nanospheres and nanocapsules or lipid vesicles of ionic and / or nonionic type.

 Such a cosmetic composition may be more or less fluid and have the appearance of a white or colored cream, an ointment, a milk, a lotion, a serum, a paste, a foam. It can also be applied to the skin in the form of an aerosol or, even, be in solid form, for example a stick or the like.

 According to an additional feature of the present invention, the cosmetic compositions, in particular the cosmetic filtering compositions, may also contain cosmetic adjuvants usually used in the cosmetics field.

Such adjuvants may be chosen from fatty substances, organic solvents, silicones, thickeners, softeners, anti-foaming agents, moisturizing agents, perfumes, preservatives, surfactants, fillers, sequestering agents, anionic, cationic, nonionic or amphoteric polymers or a further mixture of these polymers, propellants, alkalizing or acidifying agents, or dyes.

 In this regard, it will be observed, on the one hand, that as an organic solvent, it is possible to use alcohols and lower polyols such as ethanol, isopropanol, propylene glycol, glycerin and sorbitol . On the other hand and with regard to said fatty substances, these can be constituted by an oil or a wax or a

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 oil-wax mixture, with fatty acids, esters of fatty acids, fatty alcohols, petrolatum, paraffin, lanolin, hydrogenated lanolin, acetylated lanolin.

In fact, such oils can be chosen from animal, vegetable, mineral or synthetic oils. Thus, such an oil can be a hydrogenated palm oil, a petroleum jelly, a hydrogenated castor oil, a paraffin oil, a silicone oil, a purcellin oil, or isoparaffins.

 According to another characteristic of the present invention, a filtering composition, a cosmetic composition or a filtering cosmetic composition may, in addition, contain agents intended to ensure a photoprotective effect by physical blocking of the ultraviolet radiation.

 In fact, such UV photoprotective agents may be constituted by pigments and / or nanopigments of metal oxides.

 In this regard, it will be observed that good results are obtained for compositions containing nanopigments, the average size of the primary particles of which is generally between 5 nm and 100 nm, preferably between 10 nm and 50 nm. Such nanopigments may be coated or uncoated metal oxides, for example nanopigments of titanium oxide (amorphous or crystallized in rutile and / or anatase form), iron, zinc, zirconium or cerium.

 According to an additional characteristic, a filtering composition, a cosmetic composition or a filtering cosmetic composition may, in addition, contain one or more agents that filter UV-A and / or UV-B rays.

 In fact, such a filtering agent may advantageously be chosen from cinnamic derivatives, salicylic derivatives, camphor derivatives, triazine derivatives, benzophenone derivatives, dibenzoylmethane derivatives, ss, ssdiphenylacrylate derivatives, p-aminobenzoic acid derivatives, filter polymers and filter silicones.

 It should be observed that a filter composition, a cosmetic composition or a filtering cosmetic composition must, in order to be active, contain a certain percentage by weight of active substance.

 In this regard, it will be noted that such a cosmetic and / or filtering composition comprises from 0.5 to 10% by weight, relative to the total weight of the composition, of one or more nitrogenous derivatives of chalcone.

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 The Applicant has found, surprisingly, that the chemical compounds constituted by a nitrogen derivative of chalcone may, in addition and advantageously, be involved in the manufacture of fibers or textile photoprotective polymers intended to provide protection against ultraviolet radiation, in particular against solar radiation.

 In this regard, it will be noted that the invention also relates to a process for the manufacture, from a preparation, of fibers or textile polymers for protection against ultraviolet radiation, such a process consisting, at the time of one of its steps, to incorporate in this preparation, an effective amount of at least one nitrogen derivative of chalcone corresponding to the formula (1).

 Finally, the Applicant has, again, surprisingly found that the nitrogen derivatives of chalcone according to the invention could be used for the preparation of a medicament for the prevention of the harmful effects of ultraviolet radiation, such a medicament comprising at least one derivative chalcone nitrogen corresponding to formula (I).

 In the following description is given a number of examples to illustrate the invention but to which this invention is not limited.

Example 1
Preparation of the 2'aminochalcone
A mixture of 2.025 g of aminoacetophenone (0.015 mole) of 4.5 ml of 15% NaOH and 25 ml of ethanol and 1.59 g of benzaldehyde (0.015 mole) is stirred at room temperature for 24 hours. . The reaction mixture is then put at 4 ° C. for 2 hours and then the precipitate formed is filtered. It is recrystallized from methanol.

 Yield: 72%.

Melting point F = 71-72 ° C
UV (EtOH): wavelengths corresponding to the absorption maxima: # max1 = 306
Molar absorption coefficient: # = 18130

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# Max2 = 404
Molar absorption coefficient: # = 8005
1 H NMR (200 MHz, CDCl 3, 298 K): 7.24-7.87 (9H, m); 6.64-6.72 (3H, m; H 2, H 3, H 5 '); 6.31 (2H, brs; NH 2) -
Example 2
Preparation of 2'amino -5,6 benzo-2-hydroxy chalcone
A solution of 2-hydroxy-1-naphthaldehyde (2.5 mmol) and pyridinium-toluenesulphonate (PPTS) and a solution of 3,4-dihydro-1-pyran (4 mmol) in CH 2 Cl 2 (5 ml) are mixed and left behind. with stirring at room temperature for 24 hours. The reaction mixture is then washed with a 1M solution of sodium carbonate (5 ml) and then evaporated to dryness to give 2- [2- (tetrahydropyranyl) oxy] -1-naphthaldehyde (I).

 In a flask is added 15 mmol of (I) and 15 mmol of 2'amino acetophenone.

25 ml of EtOH and 4.5 ml of a 15% NaOH solution are added. The reaction mixture is stirred for 24 hours at room temperature. The reaction mixture is then added with water and then neutralized with a 1M solution of HCl and then extracted with ethyl acetate. The organic phases are washed with water and then dried over Na 2 SO 4 and finally evaporated to dryness. 2'-Amino- [2- (tetrahydropyranyl) oxy] -chalcone (II) is obtained in the form of an oil.

 The compound (II) is taken up in methanol (30 ml) to which is added 0.1 mmol of para toluenesulphonic acid. The reaction mixture is stirred for 1 hour at room temperature. This reaction mixture is added with water (15 ml) then neutralized with Na 2 CO 3 and finally extracted with ethyl acetate. The organic phases are washed twice with water dried over Na 2 SO 4 and then evaporated to dryness. The final product is recrystallized from methanol to give 2-hydroxy-5,6 benzo-2'aminochalcone.

 Overall yield: 49%.

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Melting point F = 66-68 ° C
UV (EtOH): wavelengths corresponding to absorption maxima: # max1 = 286
Molar absorption coefficient: # = 6200 max2 = 334
Molar absorption coefficient: # = 5900 # max3 = 396
Molar absorption coefficient: 8 = 11800
1 H NMR (200 MHz, CDCl 3, 298 K): 10.3 (1H, s); 7.2-8.0 (10H, m); 8.05 (1H, d; Hp, J = 15.2Hz); 7.74 (1H, d; H [alpha], J = 15.2Hz); 6.3 (2H, brs; NH 2) .Example 3
Preparation of 4-methoxy-4'N- (4-methoxybenylidene) -amino chalcone a) 1st step: preparation of 4-methoxy-4'-amino chalcone
A mixture of 2.025 g of 4'-aminoacetophenone (0.015 mol) of 4.5 ml of 15% NaOH and 25 ml of ethanol and 2.039 g of p-anisaldehyde (0.015 mol) is stirred at room temperature for 24 hours. hours. The reaction mixture is filtered, the filtrate is added with water, put at 4 ° C. for 2 hours and then the new precipitate formed is filtered off. It is recrystallized from methanol. b) 2nd step: preparation of 4-methoxy-4'N- (4-methoxybenylidene) -amino chalcone
A mixture of 1 g of 4-methoxy-4'-amino chalcone (3.9 mmol) of 3 ml of 15% NaOH and 15 ml of ethanol and 538 mg of p-anisaldehyde (3.9 mmol) is stirred at room temperature for 24 hours. The reaction mixture is then put at 4 ° C. for 2 hours and then the precipitate formed is filtered. It is recrystallized from ethanol.

 Yield: 48%.

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Melting point F = 143-145 ° C
UV (EtOH): wavelengths corresponding to the absorption maxima: # max = 358
Molar absorption coefficient: # = 40431 1H NMR (300 MHz, CDCl 3, 298 K): (s, 1H, N = CH), 6.92-8.05 (m, 14H), 3.88 ( s, 3H, OCH3), 3.85 (s, 3H, OCH3)
Example 4
Preparation of an oil / water sunscreen - an amino chalcone derivative as prepared in Examples 1 or 2 5 g - stearic acid 1 g - polyoxyethylene sorbitan monostearate 1 g - squalane 10 g - liquid paraffin 20 g - Vaseline 5 g - glycerin 15g - cetyl alcohol 1 g - stearyl alcohol 1 g - oleophilic monostearic glyceride 2 g - perfume qc - antioxidant qc - water qsp. 100 g

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<tb> Structure <SEP> Yield <SEP> Point <SEP> of <SEP> UV <SEP> (Ethanol) <SEP> 1H <SEP> NMR <SEP> Data <SEP> Appendices
<tb> (as <SEP> merge <SEP> (200 <SEP> MHz <SEP>;<SEP> CDCl3, <SEP> 298 <SEP> K)
<tb>%)
<tb>2'amino-5,<SEP> 6-benzo-2-methoxy <SEP> chalcone <SEP># max1 <SEP> = 284
<tb># = 6400
<tb> 7.1-8.0 <SEP> (10 <SEP>;<SEP>m);<SEP> 8.05 <SEP>(1H;<SEP>d;<SEP> Hss, <SE> MS <SEP> m / z: <SEP> 289 <SEP> (M +)
<tb># @@@ = 334
<Tb>

Rl=2'-NH2: R9 OCH3; 72% 67-69 C Àm'2 334 J=15,2 Hz) ; 7,74 (1H; d ; Ha, J=15,2 MS m/z : 289 (M+) R5,R6=benzo 72% 67"69 C s = 6400 Hz) ;6,3 (2H; brs ; NH2);3,7(3H;s) Anal. (CzoH17NOz) C,H,N R2=R3=R4=R7=R8= H 1 ax3 = 394 Hz);6,3(2H;brs;NH2);3,7(3H;s) Anal. (C20H17NO2) C,H,N

R1 = 2'-NH2: R9 OCH3; 72% 67-69 ° C at 230 ° C = 15.2 Hz); 7.74 (1H, d, Ha, J = 15.2 MS m / z: 289 (M +) R5, R6 = benzo 72% 67-69 C s = 6400 Hz) 6.3 (2H, brs; NH2) 3.7 (3H; s) Anal. (C20H17NO2) C, H, N R2 = R3 = R4 = R7 = R8 = H1 ax3 = 394 Hz); 6.3 (2H; brs; NH2); 3 , 7 (3H; s) Anal. (C20H17NO2) C, H, N

<tb>#<SEP> = <SEP> 12200
<tb>2'amino-2-methoxy<SEP> chalcone <SEP># max1 = 296 <SEP> 8.02 <SEP>(1H;<SEP>d;<SEP> Hss, <SEP> J = 15, 6 <SEP>Hz);<SEP> 7.75
<Tb>

2'ainino-2-méthoxy chalcone 8 - 15660 (1H; Ha, J=15,6 Hz) ;7,24-7,41 MS m/z : 253 (M+) -.,, ,=33g (lH;d;H,J=15,6Hz);7,24-7,41 MS m/z : 253 (M+) R,=2'-NH2 : R9= OCH3 ; 86% 73-75 C E = 13320 (3H; m); 7,03 (1H ; m ) ; 6,92-6,99 RI=2'-NH2: OCH3; 13320 (2H ; m ) ; 6,65-6,73 (2H ; m ) ; 6,33 Anal. (Cl6Hl5NO2)C,H,N R2=R3=R4=R5=R6=R7=R8=H a,",aX3 = 400 (2H; brs ; NHz) ; 3,92 (3H ; s) AnaL (Cl6Hl5N 2)

2'-amino-2-methoxy chalcone 8 - 15660 (1H, H 2, J = 15.6 Hz), 7.24-7.41 MS m / z: 253 (M +) -,, = 33g (1H; d, H, J = 15.6Hz); 7.24-7.41 MS m / z: 253 (M +) R = 2'-NH2: R9 = OCH3; 86% 73-75 EC = 13320 (3H, m); 7.03 (1H, m); 6.92-6.99 R1 = 2'-NH2: OCH3; 13320 (2H, m); 6.65-6.73 (2H, m); 6.33 Anal. (C 16 H 15 NO 2) C, H, N R 2 = R 3 = R 4 = R 5 = R 6 = R 7 = R 8 = H a, ", aX 3 = 400 (2H, brs; NHz); 3.92 (3H; s) AnaL (Cl 6 H 15 N 2 )

<tb> 3-- <SEP> 5-- <SEP> 11025
<tb>2'amino-2,<SEP> 3-dimethoxy <SEP> chalcone <SEP># max1 = 304 <SEP> 8,11 <SEP>(1H;<SEP> d <SEP>;<SEP> Hp , <SEP> J = 15.8 <SEP> Hz) <SEP>;<SEP> 7.77
<Tb>

ammo- , - lmet oxy cone ooo/ 70 or. s'""30700 (1H; d ; Ha, J=15,8 Hz) ; 7, 3-7,92 MS m/z : 283 (M+) R!=2'-NH2 : R8=R9=OCH3 ; 88% 72-73 C ,,,,,2= 400 (3H ; m ) ; 6,98-7,18 (2H ; m ) ; 6,7Rl=2'-NH2 : Rg=R9=OCH3 ; 11600 6,77(2H;m);6,39(2H;brs;NH,); AnaL(C,7H,7NO,)C,H,N R3=Rt=R5==R7 =H 8 = 11600 3,94 (6H ; s) Anal. (C17H17NO3) C,H,N 2'amino-2, 4, 5-triméthoxy chalcone Àmaxi -3 =306 7,88 (1H; d ; Hp, J=15,2 Hz) ; 7,78 mIz: 313 o/ '710 s =8300 (1H ; m ) ; 7,32 (1H; d ; Ha, J=15,2 MS m/z: 313 (M+) Rl=2'-NH2:R6=R7=R9=OCH3; 62% 70-71 C E = 8300 Hz) ; 7,01 ( 1 H ; s ) ; 6,75 (2H ; m ) ; Rl=2'-NH2 : R6=R=R9=OCH3 ; Àmax2 = 406 6,51(2H;brs;NH2);6,38(tH;s); Anal. (C,gH,9N04) C,H,N

ammo-, lmet oxy cone ooo / 70 gold. 30700 (1H, d, Ha, J = 15.8 Hz); 7, 3-7.92 MS m / z: 283 (M +) R1 = 2'-NH2: R8 = R9 = OCH3; 88% 72-73 C₁₂, 2 = 400 (3H, m); 6.98-7.18 (2H, m); 6.7R1 = 2'-NH2: R8 = R9 = OCH3; 11600 6.77 (2H, m), 6.39 (2H, brs; NH 4); AnaL (C, 7H, 7NO,) C, H, N R3 = Rt = R5 == R7 = H8 = 11600 3.94 (6H; s) Anal. (C 17 H 17 NO 3) C, H, N 2 'amino-2,4,5-trimethoxy chalcone at max -3 = 306 7.88 (1H, d, Hp, J = 15.2 Hz); 7.78 mIz: 313 o / 710 s = 8300 (1H, m); 7.32 (1H, d, Ha, J = 15.2 MS m / z: 313 (M +) R1 = 2'-NH2: R6 = R7 = R9 = OCH3, 62% 70-71 CE = 8300 Hz); 7.01 (1H; s); 6.75 (2H, m); R1 = 2'-NH2: R6 = R = R9 = OCH3; Λmax2 = 406 6.51 (2H, brs; NH2); 6.38 (tH; s); Anal. (C, gH, 9NO4) C, H, N

<tb> R2 = R5 = R8 = H <SEP>#<SEP> 19600 <SEP> 3.74-3.78 <SEP> (9H <SEP>;<SEP> 3s)
<Tb>

Claims (25)

1. A chemical compound consisting of a chalcone derivative, characterized in that this compound is defined by a nitrogen derivative of chalcone of general formula:

Wherein: - R1 denotes either a group NYlY2 comprising at least one nitrogen atom substituted with two groups Y1 and Y2, or a group N = CYiY2 having at least one nitrogen atom and at least one carbon atom substituted with two groups Y1 and Y2, these groups Y1 and Y2, denote, independently of one another, a hydrogen atom, a straight or branched chain, saturated or unsaturated C 1 -C 12 alkyl group, an alkenyl group, C2 to C30, linear or branched, acyclic or cyclic, an aryl group, an aralkyl group, a C6 to C30 alkyloryl group, together form a ring having from 4 to 8 atoms, such an atom being an atom of carbon and / or nitrogen and / or oxygen and / or sulfur, such a cycle may be substituted or unsubstituted, aromatic or not; or R2, R3, R4, R5, R6, R7, R8 and R9 denote, independently of each other, a hydrogen atom, a hydroxyl group, an alkoxy group, an acyloxy group or a C1-C12 alkyl group; saturated or unsaturated straight or branched chain, a nitro group, a nitrile group, a sulfur group, a phosphorus group, a chlorinated group, a brominated group, a fluorinated group, a group comprising at least one silicon atom, a group - O-glycosyl, a -O-glycosyl group substituted with one or more substituents, a C2-C30 alkenyl group, linear or branched, acyclic or cyclic, a group <Desc / Clms Page number 20>  aryl, an aralkyl group, a C6 to C30 alkyloryl group, a NY3Y4 group or a N = CY3Y4 group in which the substituents Y3 and Y4 may either independently designate one another, and on the other hand, of R 1, any of the atoms or groups of the Y 1 / Y 2 type, that is, independently of R 1, forming a ring similar or identical to a ring that may be formed by these same substituents Y 1 and Y 2 or R2, R3, R4, R5, R6, R7, R8, R9 are such that Rx and Rx + i (x = 2 to 8) together form a ring having from 4 to 8 atoms, such atom being a carbon atom and / or nitrogen and / or oxygen and / or sulfur, such a cycle may be substituted or unsubstituted, aromatic or not.  2. Chemical compound according to claim 1, characterized in that the nitrogenous chalcone derivative corresponding to the formula (I) is defined by a member of the 2'amino subfamily such as one of the following compounds: -amino chalcone; 2'-amino-2-methoxy chalcone; 2 '- (dimethylamino) -2-methoxy chalcone; 2'-amino-2-ethoxy chalcone; 2'-amino-2,3-dimethoxy chalcone; 2 '- (dimethylamino) 2,3-dimethoxy chalcone; 2'-amino-2,4-dimethoxy chalcone; 2'-amino-2,5-dimethoxy chalcone; 2'-amino-2,6-dimethoxy chalcone; 2'-amino-2,4,5-trimethoxy chalcone; 2'-amino-2,4,6trimethoxy chalcone; 2'-amino-2,3,4-trimethoxy chalcone; 2'-amino-5,6-benzo-2-hydroxy chalcone; 2'-amino-5,6-benzo-2-methoxy chalcone; 2 '- (methylamino) -2-methoxy chalcone; 2 '- (methylamino) -2-methoxy chalcone; 2 '- (methylamino) -2,3-dimethoxy chalcone; 2 '- (methylamino) -2,4-dimethoxy chalcone; 2 '- (methylamino) -2,5-dimethoxy chalcone; 2 '- (methylamino) -2,6-dimethoxy chalcone; 2 '- (methylamino) -2,3,4-trimethoxy chalcone; 2 '- (methylamino) -2,4,5-trimethoxy chalcone; 2'- (methylamino) -2,4,6-trimethoxy chalcone.  3. Chemical compound according to claim 1, characterized in that the nitrogen derivative of chalcone corresponding to the formula (I) is defined by a member of the 4'amino subfamily such as one of the following compounds: -amino chalcone; 4'-amino-2-methoxy chalcone; 4 '- (dimethylamino) -2-methoxy chalcone; 4'-amino-2-ethoxy chalcone; 4'-amino-2,3-dimethoxy chalcone; 4 '- (dimethylamino) -2,3-dimethoxy chalcone; 4'-amino-2,4-dimethoxy chalcone; 4'-amino-2,5-dimethoxy chalcone; 4'-amino-2,6-dimethoxy chalcone; 4'-amino-2,4,5-trimethoxy chalcone; 4'-amino-2,4,6-trimethoxy chalcone; 4'-amino-2,3,4-trimethoxy chalcone; 4'-amino-5,6-benzo-2-hydroxy chalcone; 4'-amino-5,6-benzo-2-methoxy chalcone; 4'- (methylamino) -2- <Desc / Clms Page number 21>  methoxy chalcone; 4 '- (methylamino) -2-methoxy chalcone; 4 '- (methylamino) -2,3-dimethoxy chalcone; 4 '- (methylamino) -2,4-dimethoxy chalcone; 4 '- (methylamino) -2,5-dimethoxy chalcone; 4 '- (methylamino) -2,6-dimethoxy chalcone; 4'- (methylamino) -2,3,4-trimethoxy chalcone; 4 '- (methylamino) -2,4,5-trimethoxy chalcone; 4'- (methylamino) -2,4,6-trimethoxy chalcone; 4-methoxy-4'N- (4-methoxybenylidene) amino chalcone.  4. Chemical compound according to claim 1, characterized in that the nitrogen derivative of chalcone corresponding to the formula (I) is defined by a member of the 3'amino subfamily such as one of the following compounds: -amino chalcone; 3'-amino-2-methoxy chalcone; 3 '- (dimethylamino) -2-methoxy chalcone; 3'-amino-2-ethoxy chalcone; 3'-amino-2,3-dimethoxy chalcone; 3 '- (dimethylamino) 2,3-dimethoxy chalcone; 3'-amino-2,4-dimethoxy chalcone; 3'-amino-2,5-dimethoxy chalcone; 3'-amino-2,6-dimethoxy chalcone; 3'-amino-2,4,5-trimethoxy chalcone; 3'-amino-2,4,6-trimethoxy chalcone; 3'-amino-2,3,4-trimethoxy chalcone; 3'-amino-5,6-benzo-2-hydroxy chalcone; 3'-amino-5,6-benzo-2-methoxy chalcone; 3 '- (methylamino) -2-methoxy chalcone; 3 '- (methylamino) -2-methoxy chalcone; 3 '- (methylamino) -2,3-dimethoxy chalcone; 3 '- (methylamino) -2,4-dimethoxy chalcone; 3 '- (methylamino) -2,5-dimethoxy chalcone; 3 '- (methylamino) -2,6-dimethoxy chalcone; 3 '- (methylamino) -2,3,4-trimethoxy chalcone; 3 '- (methylamino) -2,4,5-trimethoxy chalcone; 3'- (methylamino) -2,4,6-trimethoxy chalcone.  5. Process for the preparation of a nitrogen compound of chalcone of formula (I) according to any one of claims 1 to 4, characterized in that it consists in reacting a benzaldehyde of formula (II) on a nitrogen-containing acetophenone of formula (III) according to the following reaction scheme:

 this in a solvent selected from water, C1-C4 lower alcohols or a mixture of water and these alcohols, in a basic medium comprising an alkaline agent chosen <Desc / Clms Page number 22>  from alkali or alkaline earth hydroxides or sodium or potassium alkoxides, at a temperature ranging from 0 ° C to the boiling point of the solvent or solvent mixture.  6. Filtering composition for the protection of a sensitive material against ultraviolet radiation, characterized in that it comprises, in an acceptable support, an effective amount of at least one nitrogen-containing chalcone derivative of formula (I) according to US Pat. any one of claims 1 to 4 and constituting a compound for filtering ultraviolet radiation with wavelengths between 280 and 400 nm.  7. Cosmetic filtering composition for protecting the epidermis and / or the hairs against ultraviolet radiation comprising, in a cosmetically acceptable support, an effective amount of at least one chalcone derivative, characterized in that such a derivative chalcone consists of a nitrogen derivative of chalcone of formula (I) according to any one of claims 1 to 4 and is intended to filter ultraviolet radiation with wavelengths between 280 and 400nm.  8. Cosmetic filter composition according to claim 7, characterized in that it is intended to be applied to the epidermis and is in the form of: a suspension in solvents or fatty substances; a dispersion, in particular a vesicle, in solvents or fatty substances; a water-in-oil or oil-in-water emulsion; - A powder, a lotion, especially thickened, oily or oleoalcoholic type.  9. Cosmetic filter composition according to claim 8, characterized in that it still contains artificial tanning agents and / or browning of the skin, especially self-tanning agents.  10. Cosmetic filter composition according to claim 7 and intended to be applied to the hair, characterized in that it is in the form of a shampoo, a lotion, a gel or a composition. rinsing, before or after shampooing, before or after coloring or bleaching, before, during or after permanent or straightening, a lotion or a styling or treating gel, a lotion or a gel for blow drying or setting a hair lacquer, a permanent or straightening composition, a hair coloring or bleaching composition. <Desc / Clms Page number 23>  11. Cosmetic filtering composition according to claim 7 and intended to be applied to the epidermis and / or the hair, characterized in that it consists of a make-up product and is in the form of a cream of treatment of the epidermis and / or hair, a foundation, a lipstick stick, an eyeshadow, a blush, a liner, a mascara , a coloring gel or other.  12. Cosmetic filter composition according to claim 7 and intended to be applied to the epidermis and / or the bristles, characterized in that it consists of a sunscreen composition and is in the form of: suspension in solvents or fatty substances; a dispersion, in particular a vesicle, in solvents or fatty substances; a water-in-oil or oil-in-water emulsion; - A powder, a lotion, especially thickened, oily or oleoalcoholic type.  13. Cosmetic composition for the depigmentation of the epidermis, characterized in that it comprises, in a cosmetically acceptable carrier, at least one nitrocellulose derivative of formula (I) according to any one of claims 1 to 4.  14. Cosmetic composition for the depigmentation of the epidermis, according to claim 13, characterized in that it is in the form of an aqueous solution, hydroalcoholic or oily, an oil-in-water emulsion or water -in-oil or multiple, an aqueous or oily gel, a liquid anhydrous product, pasty or solid, an oil dispersion in an aqueous phase using spherules, these spherules may be nanoparticles polymers such as nanospheres and nanocapsules or lipid vesicles of ionic and / or nonionic type.  15. Cosmetic composition, in particular filter, according to any one of claims 7 to 14, characterized in that it still contains cosmetic adjuvants chosen from fatty substances, organic solvents, silicones, thickeners, softeners, anti-foaming agents, moisturizing agents, perfumes, preservatives, surfactants, fillers, sequestering agents, anionic, cationic, nonionic or amphoteric polymers or a further mixture of these polymers, propellants, alkalinizing agents or acidifiers, or dyes. <Desc / Clms Page number 24>  16. Cosmetic and / or filtering composition according to any one of claims 6 to 15, characterized in that it still contains agents intended to ensure a photoprotective effect by physical blocking of ultraviolet radiation.  17. Cosmetic and / or filter composition according to claim 16, characterized in that the UV photoprotective agents are pigments and / or nanopigments of metal oxides.  18. Cosmetic and / or filtering composition according to any one of Claims 6 to 17, characterized in that it also contains one or more agents that filter UV-A and / or UV-B rays.  19. Cosmetic and / or filter composition according to claim 18, characterized in that the filtering agent is chosen from cinnamic derivatives, salicylic derivatives, camphor derivatives, triazinc derivatives, benzophenone derivatives, derivatives of dibenzoylmethane, p, p-diphenylacrylate derivatives, p-aminobenzoic acid derivatives, filter polymers and filter silicones.  20. Cosmetic and / or filtering composition according to any one of Claims 6 to 19, characterized in that it comprises from 0.5 to 10% by weight, relative to the total weight of the composition, of one or several nitrogen derivatives of chalcone of formula (1).  21. A method of protecting a sensitive material against ultraviolet radiation, characterized in that it consists in applying to this material an effective amount of a composition containing at least one nitrogen derivative of chalcone of formula (1) according to US Pat. any of claims 1 to 4.  22. A method for protecting the epidermis and / or hair against ultraviolet radiation, characterized in that it consists in applying to the epidermis and / or the bristles an effective amount of a cosmetic filtering composition containing at least a nitrogen derivative of chalcone of formula (I) according to any one of claims 1 to 4.  23. A process for the depigmentation of the epidermis, characterized in that it consists in applying to the epidermis an effective amount of a cosmetic composition containing at least one nitrogen derivative of chalcone of formula (I) according to one any of claims 1 to 4.  24. Process for the manufacture, from a preparation, of textile fibers or polymers for protection against ultraviolet radiation, characterized by <Desc / Clms Page number 25>  the fact that a step of this process consists in incorporating, into this preparation, an effective amount of at least one nitrogen-containing chalcone derivative of formula (1) according to any one of claims 1 to 4.  25. Medicament for the prevention of the harmful effects of ultraviolet radiation, characterized in that it comprises at least one nitrogen-containing chalcone derivative of formula (1) according to any one of claims 1 to 4.